54885-02-8

Basic information

• Product Name: 6-Benzoylquinoline
• Synonyms: 6-Benzoylquinoline
• CAS NO: 54885-02-8
• Molecular Formula: C₁₆H₁₁NO
• Molecular Weight: 233.26
• Mol File: 54885-02-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Benzoylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Benzoylquinoline(54885-02-8)
• EPA Substance Registry System: 6-Benzoylquinoline(54885-02-8)

Safety Data

• Hazardous Substances Data: 54885-02-8(Hazardous Substances Data)

Upstream product

• 130343-63-4 (phenyl)(6-quinolinyl)methanol 
• 1144-74-7 4-nitrobenzophenone 
• 156-87-6 propan-1-ol-3-amine 
• 14002-34-7 tripropanolamine 
• 4113-04-6 quinoline-6-carbaldehyde 
• 13327-31-6 6-iodoquinoline 
• 64-18-6 formic acid 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 144-79-6 chloromethyldiphenylsilane 
• 173089-80-0 quinolin-6-yl triflate 
• 100-51-6 benzyl alcohol 
• 5145-65-3 N-benzoylpyrrole 

Downstream Products

• 130343-63-4 (phenyl)(6-quinolinyl)methanol 
• 855631-72-0 phenyl-(1,2,3,4-tetrahydro-[6]quinolyl)-ketone 

Relevant articles and documents

Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5-Diaza-3,7-diphosphacyclooctane Ligand

We report a catalytic method to access secondary alcohols by the coupling of aryl iodides. Either aldehydes or alcohols can be used as reaction partners, making the transformation reductive or redox-neutral, respectively. The reaction is mediated by a Ni catalyst and a 1,5-diaza-3,7-diphosphacyclooctane. This P2N2ligand, which has previously been unrecognized in cross-coupling and related reactions, was found to avoid deleterious aryl halide reduction pathways that dominate with more traditional phosphines and NHCs. An interrupted carbonyl-Heck type mechanism is proposed to be operative, with a key 1,2-insertion step forging the new C-C bond and forming a nickel alkoxide that may be turned over by an alcohol reductant. The same catalyst was also found to enable synthesis of ketone products from either aldehydes or alcohols, demonstrating control over the oxidation state of both the starting materials and products.

Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols

An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.

Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents

The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.